Musings of a Former Child Star Revisited
by sonkayura
Summary: We've caught a glimpse into the thoughts that keep Alvin up at night, but what about Simon? Follow-up to Musings of a Former Child Star. ONE-SHOT.


A/N: Hello friends! It has been YEARS since I have uploaded anything so this is LONG overdue and the perfect story for me to get my feet wet again! It has been in the works for some time now (understatement) and I hope you'll find it worth the wait. Just like the first story, it is based on my favorite Chipmunks incarnation, those from the newer episodes of the 1980's cartoons.

As per usual, I do not own Alvin and the Chipmunks, the Chipettes, or any of the characters mentioned in this story. I'll warn you ahead of time; there will be some profanity as well as more mature themes discussed in this one-shot. The personalities and life events of the characters are my own depiction of what I think could've happened to them in a possible future so they may not be what you expect! If you read the first story, you already kind of know, but to those that haven't, there it is!

If you feel that you may have a problem with any of this, I'd advise you to not continue further, because really, who wants to be exposed to something that's going to make them unhappy? Not me, that's for sure!

If you're cool with it all, then happy reading and please enjoy! -Nicole

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 **Musings of a Former Child Star Revisted**

The playground where they had spent many summer days as children loomed in front of him as he made his way up the hill. The nearest streetlight was a few yards down, so the space was left primarily in shadow, illuminated only by the intermittent explosions of color that detonated in the inky night sky.

When was the last time he had been here?

The hulking shapes of the equipment sat like large, sleeping dinosaurs, left to hibernate and rust in the changing elements throughout the years. It suddenly seemed like an entire lifetime had passed since he had last heard the gravel crunch under his feet, had last sat on the very swing that he had chosen to sit on at that precise moment. A wave of nostalgia washed over him as he stared out into the dark, past the orange tornado slide and what used to be the teeter totter. It really did feel like forever…and maybe that was because things were so different now.

"Shall we sit?"

Simon shook his head, being pulled from the haze of nostalgia by the girl next to him. He had forgotten she was there. He noticed with some uneasiness that she was in the exact same swing she had always sat in; third from the left, just in front of the merry-go-round.

Brittany smiled, taking the initiative as she so often did. He wondered absently if she was as weirded out about being back here as he was. If it was so, she certainly didn't show it, though this wasn't surprising.

She had changed a lot in the last few years, but her take-charge attitude was still securely intact. It was the one thing she had seemed to hold on to from her previous self; that and the inability to keep her mouth shut, even when necessary. He found this strangely comforting, especially considering most of the changes she'd made didn't sit with him well at all.

He smiled a bit as a sudden explosion of color lit her face. She almost looked younger than she was. For a second, she looked the same as she had years ago, happy and carefree, ready to take on the world.

As quickly as it had come, the image was gone with the light and she returned to the Brittany of now, the exact opposite of how he thought she would've ended up.

Her auburn hair hung around her face in stringy waves, longer than it had ever been with streaks of dark blue peeking out at her tips. The silver star-shaped stud in her nose glistened with every explosion of the sky, as well as the small hoop above her eyebrow. The only makeup she wore was an overabundance of black eyeliner and mascara, slightly smeared from the sweating she had done walking to the park from their neighborhood.

Her black t-shirt bore the name of a band Simon didn't recognize and her black capris shorts and Chuck Taylors were caked with dust and dirt. The only thing Simon found remotely familiar about her appearance were the hot pink shoelaces that glowed in the darkness of the playground.

Once again, he found himself shocked at how things had turned out. If somebody had come up to him three years ago and said that Brittany Miller would look like this, he and everyone he knew would've gotten a good laugh. That wasn't the craziest part though. The biggest difference about her by far, was her eyes. They were still the same color, but they weren't the same eyes.

The eyes of the Brittany he knew had been bright, happy, and confident. She had always used to brag about how her eyes sparkled more than anyone else's, usually resulting in an argument from Alvin. Now, it was as if somebody had blown out a candle inside of her. The former glow that they had held had been replaced by an emotion all too easy to recognize. Sadness.

 _How did it come to this?_

Simon placed his elbows on his knees and looked down at his feet, running his fingers through his hair, now slicked in a thin layer of sweat. The night was hot, muggy, and the air was thick with moisture and mosquitos. Typical weather for a night in July-the 4th to be exact.

Brittany turned away from him, reached into her pocket, and pulled out a package of Marlboro Lights as well as a neon-orange lighter. Taking a cigarette from the package, she placed it between her lips, lighting it as she went. She then looked at Simon, holding the pack to him.

"I know you don't smoke, but have one with me. We're here; it's the Fourth, you only live once and all that bullshit. I think it's appropriate."

Simon stared at the pack, contemplating what to do. All of his life he had always been the" good child." He had never been in trouble, never gotten below an A minus on anything he had ever done in school, never really broken the rules period. He had always been the sensible one. The voice of reason. The one whose job it was to keep things in order. He had responsibilities and it was his duty as a functioning human being to fulfill them to the best of his ability. He didn't just do what was expected of him, he did more. He made it a point to always be responsible, dependable, reliable, and prepared for whatever life would potentially throw at him. He did everything RIGHT and wouldn't cease his efforts until there was as little room for failure as possible. It was what was expected of him and he delivered every single time. While his brothers, namely Alvin, were goofing off, sleeping, and partying the summer before their senior year away, Simon was hard at work taking a full schedule of summer college prep courses, as well as working at the public library on the weekends and most evenings. He had his head on straight and knew where he was going.

And it was fucking exhausting.

Sure, there had been that one unfortunate incident with the piano, but that had been mostly Alvin's idea, not his. He, as usual, had been dragged along for the ride and had gotten caught up in all of the craziness of his brother's antics. In fact, the only times he had EVER been in trouble in his entire life had been because of something Alvin had cooked up.

Not that any of that mattered now. He and his brother rarely spoke anymore unless it was about something mundane like, "do you know where Dave hid my car keys?" or "the Wi-Fi is fucked up, can you fix it?" That was basically the extent of their relationship at this point, and Simon was fine with it. The less he associated with Alvin, the less likely he was to have issues later on. It was proven in everyday life as far as he was concerned!

His whole life, he had felt tremendous pressure to succeed in what he did best… and he had! He had never slipped up, not even once. He was positive that nobody would ever predict he would even contemplate smoking a cigarette. He would even be considered a hypocrite, considering he had spoken out against smoking numerous times.

Something so simple and miniscule would surely ruin everybody's perception of him…however tonight, he didn't care.

Brittany was right. You only live once and Simon felt way overdue to do something rebellious and out of the ordinary. He absolutely didn't intend to make a habit out of it, but for tonight…tonight, he wasn't going to be "good Simon." Tonight, he was going to live, starting with this cigarette.

Reaching out, he took one from the pack, allowing her to light it for him. Immediately, he began to cough as the smoke filled his lungs. Brittany laughed.

"You're not supposed to swallow it genius."

Simon sputtered, laughing along with her.

"Pardon me, but I'm a cigarette virgin," he said, "It's gonna hurt a few times before I get comfortable." Brittany continued to laugh.

"Well, consider your cherry popped."

Simon nodded, taking another puff. This was a bit better. He could possibly get the hang of it, at least for this one time.

The two sat there in silence for a moment, taking in the atmosphere and the night, Brittany once again being the first to break the silence.

"Sorry, but I had to get the hell outta there. I could feel my IQ dropping every second I had to sit there, watching the douchebag brigade blow up Barbies like a bunch of ten-year olds. Seriously, my already fragile brain couldn't take anymore."

Simon pushed his glasses further up on his nose. Once upon a time, the 4th of July had been his favorite holiday. The whole neighborhood would gather together in the street for a giant block party with lots of food, fireworks, and water balloon fights. He and his brothers would be out well after their usual bedtime, running up and down the street with Brittany, Jeanette, and Eleanor, laughing and chasing each other under the multicolored sky. It was as close to magical as he had ever experienced and they were some of the happiest memories of his childhood.

Now, all of that felt alien, as if someone else had lived those times and he was merely watching a playback of their life. It didn't even feel real anymore. Sure, some of the same elements were still present. The neighborhood block party still happened, but there was notably less excitement, and it had turned into something that he dreaded rather than looked forward to all year. It was agonizing and tonight had definitely been one of the worst.

About two hours into the party, two cars full of Alvin's friends, as well as Jeanette's, had invaded the street, bringing a Rubbermaid container full of old toys and Black Cats as well as a whole barrel of obnoxiousness and immaturity to go along with it.

Shortly after their arrival, they had begun their own personal demolition derby in the midst of what was supposed to be the most fun night of the year. Simon couldn't kid himself though; it hadn't been "most fun night of the year" in a long time.

For the past three years, his Fourth had consisted of remaining on the porch with the grandparents, pretending to be interested in topics like golf, who was dying and who was fighting about it, and the newest arthritis medications. The only time the conversation got even remotely interesting was when the subject of politics was brought up, though that was usually short lived considering Grandpa Seville's overzealous opinions on certain topics, usually having the opposite viewpoint of Simon. That was generally his cue to leave, which would of course result in a dirty look from Dave. It had been all but excruciating and before he knew it, his once favorite day of the year had turned into his least favorite by far.

This year however, Brittany had approached him, offering a proposition. Unsurprisingly, she had wanted to escape the theatrics that were going on in front of their very eyes as well, suggesting that they walk up to the playground for a bit of a "nostalgia trip."

Simon had agreed, all too happy to escape from the chaos in the street and the conversation Dave was having with Grandpa Seville about his recent bowel obstruction scare.

He didn't realize just how great the nostalgia would be once they had reached this spot. Despite the shitter that the Fourth was now, so many good memories were attached to this day, as well as some pretty hilarious ones.

Simon recalled one such event in particular when they had been about seven or eight. Dave had bought a package of one thousand sparklers, since they always seemed to be in short supply, especially since Teddy had had a tendency to constantly submerge them in the birdbath over and over again.

Alvin, being the showoff that he was, had insisted on having two sparklers at the same time since he had seen Brittany doing it just a few minutes prior. It had always been a competition with those two and Simon was certain this was a recipe for disaster, especially since Alvin lacked majorly in the self-control department.

Dave had of course said no, stating that Alvin didn't need two sparklers that it was dangerous, and all of the other warnings parents give their children when they sense potential disaster.

Alvin of course, had never been good at listening to Dave and once his back was turned, took it upon himself to light another one with the tip of the other. He hadn't been expecting such a large spark and it had startled him, the sparkler flying out of his hand and right down Dave's sock.

Needless to say, Alvin had spent the rest of the night in his room.

Simon chuckled a bit; he hadn't thought about that in forever.

"Penny for your thoughts?" Brittany asked.

Of all of his former friends, Brittany was surprisingly enough the one he'd managed to remain closest to. Despite her like for fighting and smoking, they had a lot of the same friends, as well as the same interests. This was once again something he never would've predicted years ago.

In a way, he felt as if they had almost gone through the same thing. He wasn't ready to admit outright that he felt abandoned by Jeanette, but he knew that Brittany felt the same way about Alvin. Even though they had argued and competed with each other constantly, having a "love-hate" relationship if you will, Simon had always felt that they had been put on this earth as a pair. Perhaps the hurt inflicted by Alvin had caused Brittany to act the way she did now. Simon didn't know the whole story of what had happened between them, but he did know that Brittany could hold a mean grudge. He was pretty sure that the reasons for her actions ran a bit deeper than just normal teenage drama.

Pulling himself out of his thoughts, Simon looked at Brittany, taking another puff from the cigarette.

"It's just weird being here, you know?" Brittany nodded, looking out at the playground.

"I know," she agreed, "I drive passed here at least once a day and I always look. I try not to, but I always do. "

"Me too," said Simon, "It's almost subconscious. We have a lot of good memories here." Brittany nodded.

"Yeah, but I try not to think about those any more than I can help it…" She looked down at the ground. "Just reminds me of what we aren't anymore, you know?"

Simon didn't respond, but looked away towards the houses bordering the left side of the playground. He agreed with Brittany one hundred percent, but wasn't ready to admit it just yet. It was easier to put on a tough exterior and act like he didn't care. With that, he shrugged.

"I don't know. Things change, people change," he took another drag on the cigarette. Brittany looked at him, her blue eyes searching. Simon knew she was trying to read between the lines. He silently wished her luck with that one. If anybody was good at hiding what they truly felt, it was Simon. He had been doing it his whole life, not just now.

This charade had begun way before his teenage years were even a faint light on the horizon. He knew he had issues, he was far too educated and aware of himself to think otherwise, but admitting it to anyone else was out of the question at this point. He had been the only one not to attend counseling once Dave had subsequently ended their music career, as it hadn't affected him in the way it had affected Alvin for example.

Truth be told, Simon had loved singing with his brothers, but always knew his true interests lay elsewhere. Rather than being depressed about the end to their entertainment career, Simon had embraced it and had looked at it as an opportunity to explore other avenues of his life. Singing backup to Alvin wasn't his life's goal, therefore the end had been looked at as a new beginning by him, just as Dave as suggested at the time.

Theodore had taken it in a mixed way. He had been sad, cried, and even joined in Alvin's attempted persuasion of Dave to let them continue singing. However, once it was all said and done, he too began to realize that there was life after The Chipmunks. Theodore had always made friends very easily and found comfort in his continued love for food. He had told Simon on numerous occasions that he wouldn't mind going to school for culinary arts once they graduated and Simon had encouraged him in every way possible. He wanted nothing more than for his brother to follow his dreams and find other things he liked about himself, other than the music.

The only one who hadn't embraced this was Alvin, which may have played a large role in the way his brother behaved. As far as Simon was concerned, Alvin could do what he wanted. He would anyway, so why try to encourage him differently? Yes, it put a strain on their household, but that's why he lived in the basement. It was easy to get away from everything if he just remained out of sight, much like he always had.

"Simon, you with me here?"

Once again he was pulled from his thoughts by a smirking Brittany. He smiled at her.

"Yeah, sorry. God, I can't focus tonight…" Brittany laughed, throwing her cigarette butt on the ground and squashing it with the toe of her shoe.

"I can never focus, so I'm right there with ya," she said. Shifting a little on the swing, she turned to him. "No, seriously though," she asked, "What's up? You gotta have something on your mind if you keep zoning out on me."

Simon shrugged. He wasn't a heart to heart kind of guy, but he had agreed to come up here with her. He couldn't just stare ominously into space like a bad CW drama. He should at least try and make conversation. It was just Brittany after all.

"You ever wake up and think, 'what the hell happened and when?'" Brittany nodded.

"All the time. Why?"

Simon shrugged.

"I'm just constantly amazed at how things turned out. I mean, the six of us were inseparable and now, it's like we all live on different planets."

"You're talking specifically about Jeanie aren't you?"

Simon was startled at that. He hadn't expected Brittany to bring up Jeanette so soon. He knew she would eventually, but right off the bat? This had caught him off guard and he wasn't sure all of this talking was such a good idea. She must've sensed his discomfort because she spoke up almost immediately.

"Simon, I want you to know that whatever is said here tonight," she gestured to the playground, "doesn't leave this space. We're talking as friends and I'm not gonna go blab to Jeanette everything you say. So don't be afraid to speak up."

Simon turned to look at her, knowing she was telling the truth. Contrary to what everyone may believe of what impression Brittany gave, she was very good at keeping secrets and meant what she said. There was no bullshit with her, and Simon appreciated that. Feeling a bit better, he responded.

"Honestly, it still surprises me you and Jeanette are still as close as you are." Brittany laughed.

"I can't explain it either. I know she's changed a lot, but she's still my sis you know? A big part of it I think is Ellie. She keeps us from tearing each other apart."

Simon nodded. The fact that Jeanette had changed "a lot" was the understatement of the year in his eyes. More like, "normal" Jeanette had left the planet and had been replaced by "gluten-free, yoga-guru, makeup-wearing, super spunky cheerleader" Jeanette." That was his theory anyway. His former best friend had done a complete 180 degree swap from who he once knew. She had come back from camp that summer and had completely…transformed. All of a sudden she had a whole new set of goals, a whole perspective on herself, and a whole new set of friends.

Not that he wasn't happy that Jeanette was happy with herself now, he was! He recalled many times before that she had confided in him about her insecurities, always feeling inferior to her sisters, always feeling like she was destined to remain in the background. He had seen the way she looked at Brittany, with her confidence and good looks, and popularity. He knew that that was something Jeanette had always wanted for herself, but had had no idea how to obtain. Then, within four short weeks, all of that had changed.

It was like they had switched places. And it had unfortunately resulted in him losing his best friend, something that he didn't know he would ever be able to forgive her for. But he couldn't say all of this to Brittany, at least not in so many words. After all, Alvin had put her through something very similar.

Simon looked at Brittany and smiled.

"Well, I know that if you would've told me five years ago that we would be having this conversation, I probably wouldn't have believed it, at least not right away."

Brittany laughed, a short harsh laugh, followed by a cough. Simon flinched and looked down at his cigarette, the end no longer glowing. _Eh, I'll take that as a sign…_ he thought to himself and threw it on the ground, stomping it with his foot to make extra sure that it was out.

Brittany stared up at the sky as yet another explosion lit the area.

"Yeah…me too," she agreed. Simon looked at her, her profile barely visible next to him. She looked sad. Like someone who was thinking of the things that made her the saddest in the world, and she was processing them without crying.

"Hey Brit," he said, and she turned to face him. Licking his lips, he met her eyes and told her exactly how he was feeling, something he hadn't done in a very long time.

"I guess I just don't get what happened with Jeanette. I mean, I get that she wanted to better herself and do what makes her happy and I fully support that, don't get me wrong. But…I just don't understand why she had to change absolutely EVERYTHING. All of a sudden, she just didn't have time for me or our friendship and …"he paused, trying to think of the proper way to word what he was saying. Jeanette's behavior had completely stumped him and he didn't like that feeling; it was not something he was used to and he felt the intense need to remedy that fact. Brittany sat back and continued to look at him.

"You want to know what's funny?" she asked, a certain amusement in her voice, "I feel the same way about your stupid brother."

"I know. I don't get what happened to them! Or to any of us! Every time I see Jeanette, I think of a hundred things I'd want to say to her and for some reason, I never do. Not that she'd probably stick around long enough to hear anyway…" Simon had tried to talk to Jeanette numerous times in the beginning. He'd wait by her locker at school, send her messages on her phone and email, hell, he had even physically knocked on her door a few times. Sure, she had spoken to him briefly if she had to, but it was never anything to take note of. She just seemed simply too busy for him and eventually, he had given up, but not before packing away a healthy dose of bitterness and resentment to take along for the ride.

The parallels between what had happened between he and Jeanette as well as Alvin and Brittany were almost scary and Simon had spent many nights awake, comparing and pondering what may have caused these changes. Even Eleanor and Teddy's relationship had changed, though not in as severe a way as the others.

From what little he had learned from Brittany, Ellie resented the fact that Teddy had begun dating Jenny Smith, a girl at school that was heavily involved in the drama department with Teddy and Ellie. She and Ellie had never really gotten along, mostly due to competing over lead roles in the plays and solos in the varsity choir concerts, and when Teddy had starting dating her, apparently that had caused the rift for further widen.

Brittany blamed the fact that Ellie had never told Theodore how she felt, but Simon wasn't entirely sure that his youngest brother was as oblivious to his friend's feelings as Brittany seemed to think he was. Simon speculated that the fear of ruining the friendship, as well as any other repercussions that may have come with dating each other, had scared Teddy off and dating Jenny was sort of like a security blanket. That and he had other speculations about Teddy that he hadn't shared with anybody else; it wasn't his place to go broadcasting his brother's business, but he was almost 99% sure that he was correct.

The few times Jenny had been to the house in the year they had been dating, she and Teddy had seemed more like good friends than boyfriend/girlfriend, at least on his end. Not once had he ever witnessed them being affectionate, even hand-holding had never occurred where he could see it. And Teddy hugged everybody! He was a hugger and he had never seen him hug his girlfriend! There had been one instance in particular that he recalled at the moment from not long ago.

Simon had been downstairs in the kitchen making ramen and Jenny had come storming out of the basement, purse in hand and a scowl on her face so severe, it even made it him flinch! Teddy had come bounding after her, pleading with her to stop to no avail. She had left in a huff and Teddy had stormed up to his room, not bothering to give an explanation or say anything about what had just happened. It definitely wasn't like his brother to "storm" anywhere, which led Simon to believe they'd just had a fight of some kind.

Alvin, ever the captain obvious of the three, had chimed in from the table where he had been sitting on his laptop.

"Bet he wouldn't give her any. That chick is STARVED. I can smell it. I try to tell him, but all he does is tell me to mind my business," Alvin had tsked tsked and stood, closing the laptop and grabbing his car keys, "He'd better figure it or she's gonna find someone who will. Trust me, I know a few guys that would line up. She's hot for a theatre chick." And with those final "words of wisdom," he had disappeared out the door.

As much as Simon had wanted to rub it off as the usual bullshit Alvin spewed on a regular basis, the more he thought about it, the more his brother had a point, however moronic he had put it. Sure, Simon wasn't an expert in the girl department, but he had dated Jillian for almost three and a half years and knew a thing or two about physical intimacy. Correction. He knew a LOT about it, not necessarily from experience (though he did have a larger amount of that than he was sure Alvin thought), but also from his studies and reading. And from what he could tell, that part of Teddy and Jenny's relationship was more or less non-existent.

Simon hadn't let his thoughts linger on his brother's romantic life for long-he just saw certain signs and traits that led him to believe that Teddy was probably still learning about himself and that was okay! Whatever his brother decided or whatever the future held for him, Simon would support it no matter what. Until then, he'd sit back and let Teddy handle his own affairs and if he need Simon for something, he knew that he would ask and Simon would be there, ready to help in any way.

With that, Simon seemed to jolt back to reality. How quickly his thoughts had strayed from Jeanette to Teddy, he didn't know, but he was pretty sure it was because Brittany had mentioned Ellie. Regardless, he hoped everything worked out for them. It felt pretty shitty losing Jeanette. He didn't want Teddy to lose Ellie completely too, mostly because he felt like they were going to need each other in the near future.

"You zoned out again."

Brittany had spoken up from next to Simon, another cigarette in hand, looking at him expectantly. Simon smiled.

"Yeah…sorry about that. I don't know. I'm honestly just ready to graduate next year and get the hell out of here."

Brittany nodded in agreement.

"You and me both," she then turned to look at him again, swatting idly at a fly that had been buzzing around her nose.

"For what it's worth," she started, "I'm sorry about Jeanie and how she's treated you the last three years. I've told her how fucked up it is, but she just says that people change and makes an ass load of excuses. It's a cop-out if you ask me. But I think one day she's gonna wake up and realize how stupid she was and come crawling back and who knows if you'll even be there because your life is going to be moving forward. And she'll be stuck here, trying to avoid the past when really, it's the whole reason for the absolute shit pile that everything has turned into." She looked away, taking a deep drag on her cigarette and blowing the smoke out slowly.

Simon stared at her, knowing that the second half of that statement was more about her and less about him, but he let it rest. He knew how badly Alvin had hurt her and in the beginning, he had questioned his brother about it to not avail. Alvin had said similar things that Jeanette had supposedly said (which stung worse than Simon thought they would), that people change and grow apart. However Simon knew better. Alvin and Brittany hadn't grown apart. He had abandoned her.

Simon shook his head and began to rock and forth on his swing.

"You know what I think?" he said.

"What?"

Simon turned to look at his friend, his unlikely ally in this whole crazy mess that their teenage lives had turned into.

"I think we've been sitting her, rehashing the past and wollowing in our own self-pity for too long. It's the 4th of July and it already sucks, so let's turn it into something that kicks ass, just like back in the day."

Brittany looked at him, puzzlement written all over her face.

"What are you getting at Simon?" Simon grinned.

"Remember one of our favorite parts of the 4th back in the day were the water fights we used to have? Well, I think we need to bring that tradition back."

Brittany looked at him, a slow smile creeping across her features.

"I'm listening…"

Simon stood up, brushing his hands on his pants.

"It's hot out and I think everyone on the block could do with some cooling off tonight. Wanna hit up Walmart and stock up on water balloons?"

Brittany's face not only lit up from the continuing fireworks in the sky, but also in amusement and anticipation.

"I'll drive."

Simon offered her a hand and Brittany took it, standing up and putting her cigarette out with her foot. Together, they made their way out of the playground and to the trail that would lead back to their neighborhood.

The sky continued to sparkle as he recalled the last few years of his life, the events seeming to flash in front of him like a moving picture, never stopping and always changing. Sometimes he wondered if he was still on the same planet. Sometimes he felt like the only one who still was.

And honestly? That was fine with him.

END

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Thank you all so much for reading. Please review if you like!


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